تفاعل #6338

معادلة التفاعل

diethyl 2-acetoxyethoxymethylphosphonate

sodium ethoxide

→

title compound

المردود 70.0%

Diethyl 2-hydroxyethoxymethylphosphonate

المردود 70.0%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe solution was filtered immediately
2. 2
   غسيلthe resin washed with ethanol
3. 3
   أخرىthe combined filtrates evaporated under reduced pressure
4. 4
   أخرىThe residue was chromatographed on silica gel (eluted with chloroform: methanol, 98:2)

الإجراء التجريبي

To a solution of diethyl 2-acetoxyethoxymethylphosphonate* (16 g, 63 mmol) in absolute ethanol (150 ml), was added 0.5M sodium ethoxide (12.19 ml). After standing at ambient temperature overnight, 1R-120H resin was added until pH 6.5 was reached. The solution was filtered immediately, the resin washed with ethanol and the combined filtrates evaporated under reduced pressure. The residue was chromatographed on silica gel (eluted with chloroform: methanol, 98:2) to yield the title compound as a colourless oil (9.3g, 70%). IR: νmax (film) 3420, 3000, 1450, 1395, 1240, 1170, 1130, 1030, 970 cm-1. 1H NMR: δH (CDCl3) 1.35 (6H,t,J=7Hz, (OCH2CH3)2), 3.75 (4H,br.s, OCH2CH2O), 3.90 (2H,d,J=8Hz, O--CH2P), 4.20 (4H,m,(O--CH2CH3)2), 5.20 (1H,br.s, D 2 O exchangeable, OH). Found: C,38.64; H,8.27%. C7H17PO5.0.3H2O requires: C,38.63; H,8.01%.

المصدر